Ethers of z-butyloc



Patented Mar. 2, 1954 SAME Milton Kcsmin, Dayton,

santo Chemical Compa poi-ation of Delaware No Drawing. Application August 14, 1950,

Serial No. 179,3 Claims. (01. 260-615) The present invention relates to compounds having high surface-activity in aqueous solutions and to'xprocesses for preparing the said compounds. v I I In my prior Patents Nos. 2,508,035 and 2,508,036 issued-May 16, 1950, I have disclosed polyglycol ethers of certain branched chain alcohols, namely, 5-ethyl nonanol-2 and Z-n-propyl heptanol. These products are produced by condensing ethylene oxide with the respective alcohols. While these compounds showespecially low and therefore advantageous wetting-out speeds when aqueous solutions thereof are tested by the Draves test, these products have been found to be somewhat deficient ln detergency.

I have now found that if at least 5, but less than 21, moles of ethylene oxide be condensed with 2-butyloctanol-1 that a series of products is obtained which exhibit not only excellent wetting out properties but also excellent detergency. As a matter of fact, the detergency of the present products is superior to that of the corresponding products made from n-dodecanol.

Relative detergency may be measured by any quantitative method; however for the purpose oi evaluating the present and related products I ,have used the method described by Jay C. Harris "in Soap and Sanitary Chemicals for August and September, 1943. By the application of this method it is possible to evaluate the dctergency of a product in terms of any standard detergent. For convenience I have compared the detergency of the present and related products with the detergency of Gardinol, which is a commercial detergent product produced by sulfating the alcohols derived by hydrogenation of coconut oil fatty acids.

The detergency 01 the present and related products as determined by the Harris method is illustrated in the following table:

-BUTYLOC- OF MAKING Ohio, assignor to Monny, St. Louis, Mo., a cor- TENT OF BOLYGLYCOL ETHERS OF 2 TANOL-l AND PROCESS Detergency, Percent of Gardinol Product Tested I 100% Active Built 1 M 300 50 300 p.p.m. p. p. m. p. p. m. p. 11ml \M Lorol +10 moles ethylene oxide 112 112 1 Lornl +15 moles ethylene oxide. 106 109 1:3? 2-n- Pr0pylh eptanol+5 moles etnylcne oxide 50 45 111 106 2-n-Propylhcptanol+l0 moles ethylene oxide 78 09 109 2-n-Propylhcptanol+l6 moles ethylene oxide 102 87 93 109 5-Ethylngnanol-2+5 moles ethylene ou 6 s. 3 5-Ethylnonanol-2-l-l0 moles J 37 106 ethylene oxide 114 110 111 5-l%1th1ylnonaanol-2+l5 moles e 1y ene 0x1 e .110 101 2-Brllztylogtanol-l+fi moles ethyl- 101 116 s e on e .1 "9 42 2-But1yloctaol-l+7.5 moles o 100 65 e y sue on e 102 93 12 2-Butylqcitanol-l+l0 moles othyl- 7 136 ene on e 107 110 3" 1 Z-Butylqctanol-l-l-lfimolesethyl- I a 43 ene oxide 102 93 129 126 1 The builder consisted of 40 40 parts of starch for each 20 parts 1 Cocoanut oil alcohols.

The present parts of tetrasodium pyrophosphate,

of the active constituent.

products are prepared by condensing et ylene oxide with 2-butyloctanol-1 until at least 5 mol been cond densation oxide eith heating t The cond es, but not in ensation reacti excess of 20 moles, have The conon is aided by the presence of a catalyst. For this purpose any alkaline materials, such as an alkali metal hydroxide or alcoholate may be used. The catalyst may be employed in relatively from 0.5% to 1% being small amoun usually employed. The catalyst 2'-butyloctanol -1.

is, added to the liquid alcohol at the beginning'ot the reaction.

The products so produced are secondary alcohol ethers and are believed to have the structure:

CH2CH2CH2CH:

CHICHiCHEOHlOHlCHQCHCHI (zHAOMCaIEhOH where n is an integer having a value of from 4 to 19.

4 What I claim is: 1. Compounds having the formula:

OHzCHaCHzCH;

CHaCHaCHzCHzCHnCHzCHCH:

t ((ID:H4O)"C2H4OH where n has a value of at least 4 but not in excess of 20.

2. Compounds having the formula:

The following examples will further illustrate oHzcHflcHiom this invention: omomomomomomonom EXAMPLE 1 I!) 1) 141.0 g. (0.756 mole) of Z-butyloctanol-i was 2Hl )4 2H4OH placed in a glass flask, 2.6 g. of powdered KOI-I 3. Compounds having the formula: added and the contents then heated to 120 C. 0320320112053 A stream of gaseous ethylene oxide was passed into the alcohol. by; means of? a. gas dispersing; tube and tliestream continued until 16710 g: of

CHaCHzQHaCHzCH: CH2. QHa

ethylene oxide had combined. The mass became hot due to the exothermic reactionheati and the temperature was controlled by. cooling, m" Compounds having the formula" the flask by the application otfcold Water. toythe' OHzOHzCHzCHQ exterior. In this way the temperaturewas maincmomemomomomoncnz tained at about 150 during the progress of the reaction.

The product obtained correspond'sto the=penta=- no (C2H40)14C2H40H ethylene glycol ether of 2-butyloctanol-1.

EXAMPLE 2' A portion of the product obtained. above, weighing 208v g., was further treated with 5'6= g: of ethylene oxide using thesame apparatus as described above- There was thus obtained a 7-.5: 1 molan; ratio. ethylene. oxide-Z-butyloctanol- 1 condensation product.

EXAMPLE 3 A. portion of. the: product obtained in Example 2; weighing 191- g., was further treated with 41 g: ofethylene oxideusing the same apparatus" as; describedabove. The product obtained cor responded to the decaethylene glycol ether" of EXAMPLE 4' Draves test of the products when dissolved:v in:

water tdforma 0.5 solution gave. the following. values:

The process" which comprises passing ethylene oxidez into: Ze-blltYlOCtfiIlOl-l at a temperature; of from 110 c. to 170 0. until at least 5 moles, but less than 21 moles, of said ethylene oxide have combined with each mole of said 2-butyloctanol-1.

men:

References-.- Gitedi; the file ofi patent:

UNITED STATES PATENTS Number; Name Eaten 1.69.6,314; Young. Dec. 25,. 1921i- 1,270,578 Schoelleneta1. Aug... 2.1 1934 2,226,119. De Gmoteet a1. .Dec..24,-, 19. 40

5; 2 316,842 Coleman Apr. 20,. 1943. 2,355,823. Schlegel. Aug..15,, I944! 2,491,533. Sworn; Dec. 20,. 1949. 2,508,035 Kosmim May, 16,]. I950 2,5118936. Kosmin. May. 16,. 1950.

Table- Spec-dot." PifOdilOtlTQStGd. Wetting, Seconds Eiiamplecllnuflnu 2.6. Example 2 2.. 9. Example 3'... Instantaneous. ExammeaQ 214. LoroLH-ldmoies ethylene oxide 10. 9. ljoroTH-l-fi'moles ethylene oxide 30'. 8.

Sokol' out. 31. 1950 

1. COMPOUNDS HAVING TE FORMULA: 